US4904274A - Coloring hair with aminoalkyl-or aminohydroxyalkyl-catechols - Google Patents

Coloring hair with aminoalkyl-or aminohydroxyalkyl-catechols Download PDF

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Publication number
US4904274A
US4904274A US07/193,694 US19369488A US4904274A US 4904274 A US4904274 A US 4904274A US 19369488 A US19369488 A US 19369488A US 4904274 A US4904274 A US 4904274A
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United States
Prior art keywords
nhr
hair
sub
aminoalkyl
aminohydroxyalkyl
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Expired - Lifetime
Application number
US07/193,694
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English (en)
Inventor
Thomas M. Schultz
Leszek J. Wolfram
Keith C. Brown
Giuseppe Prota
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P&G Hair Care Holding Inc
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Clairol Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Assigned to CLAIROL INCORPORATED reassignment CLAIROL INCORPORATED ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BROWN, KEITH C., PROTA, GIUSEPPE, SCHULTZ, THOMAS M., WOLFRAM, LESZEK J.
Priority to US07/193,694 priority Critical patent/US4904274A/en
Application filed by Clairol Inc filed Critical Clairol Inc
Assigned to CLAIROL INCORPORATED reassignment CLAIROL INCORPORATED ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BROWN, KEITH C., SCHULTZ, THOMAS M., WOLFRAM, LESZEK J., PROTA, GIUSEPPE
Priority to CA000573005A priority patent/CA1325772C/fr
Priority to MYPI89000211A priority patent/MY104950A/en
Priority to EP89301919A priority patent/EP0341808B2/fr
Priority to ES89301919T priority patent/ES2056202T3/es
Priority to DE68916319T priority patent/DE68916319T3/de
Priority to AT89301919T priority patent/ATE107500T1/de
Priority to JP1052186A priority patent/JPH01290618A/ja
Priority to KR1019890006359A priority patent/KR950005117B1/ko
Publication of US4904274A publication Critical patent/US4904274A/en
Application granted granted Critical
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/20—Halogens; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes

Definitions

  • This invention relates to an improved process for dyeing hair on the human scalp or head that utilizes certain aminoalkyl or aminohydroxy alkyl catechols as the essentially sole chromogenic agent with or without color modifiers such as phenylenediamines, nitrobenzenes or similarly used direct dyeing agents common in the art of coloring the hair. More particularly, the invention relates to the use of certain metal ions as catalytic agents for an efficient in situ conversion of said chromogenic agent to melanin-like, durable dyes, whereby certain deficiencies in the procedures previously reported are markedly reduced.
  • aminoalkyl- or aminohydroxyalkyl catechols that are useful for the purposes of this invention are more particularly described by the formula. ##STR1## wherein
  • R 1 is H or OH
  • R 2 is H or alkyl
  • n 0 or 1.
  • R 2 is alkyl, it is preferably, a lower alkyl radical having from 1 to about 4 or 6 carbon atoms.
  • a procedure which has been suggested in the prior art for hair dyeing involves the use of an aminoalkyl catechol in a non-alkaline solution containing an oxidizing system.
  • This is exemplified by European Pat. No. 161073A of 1984 which claims a process of dyeing hair with, e.g., dopamine in a combination containing iodate and a persulfate or periodate. It is said to dye hair pleasing shades of brown and black. However, this requires a treatment that takes over 60 minutes.
  • U.S. Pat. No. 4,453,941 to Jacobs relates to a process for producing pigmentation in hair or on skin. This process involves treating hair with a reaction product of, for example, N-acetyldopamine and an omega amino acid.
  • a reaction product of, for example, N-acetyldopamine and an omega amino acid In column 3 beginning at 47, the patentee describes a process wherein lengths of gray human hair were soaked with a 0.1M copper chloride solution. The hair is then rinsed and soaked at 25° C. with a mixture of 0.01M N-acetyldopamine and 0.1M beta-alanine. The hair is said to assume a golden blond color.
  • This disclosure is different from the present invention in several significant respects. In the first place, the N-acetyldopamine employed is not a compound that falls within the definition of the formula I compounds that are useful for the purposes of the present invention.
  • N-acetyldopamines are known to undergo indolization reactions very poorly which limits their ability to give melanin-like materials. As a result, under most dyeing conditions, they produce only low intensity dyeouts of light shades.
  • Jacobs patent requires, as a matter of necessity, the inclusion of an amino acid such as beta-alanine in the treatment composition.
  • an amino acid such as beta-alanine
  • Jacobs goes to great pains to point out that his coloring agent is a reaction product of the N-acetyldopamine and the beta-alanine. This is clearly quite different from the case of the present invention wherein there is no necessity that the compound I components be reacted with a second compound to generate the color producing agent.
  • Japanese Pat. No. 50130443 teaches a three step process for coloring hair involving:
  • the process of the present invention in its broader aspects visualizes that the metal ion and the formula I compound may be applied to the hair either concurrently or sequentially. However, in the preferred mode of practicing the process of this invention these will be applied sequentially, the metal ion being applied to the hair first.
  • this sequential treatment also includes the case wherein the metal ion pre-treated hair is dyed with a composition containing both the formula I compound and another metal ion (e.g., those demonstrated in Examples 13, 15, 16 and 18).
  • any compound falling within formula I above would be useful in the practice of the present invention.
  • Dopamine 3,4-dihydroxyphenylethylamine
  • epinephrine 3,4-dihydroxybenzylamine
  • 2-hydroxy-2-(3,4-dihydroxyphenyl)ethylamine i.e. ##STR2##
  • the formula I compound will usually be applied to the hair from a hair dye composition containing the same.
  • This hair dye composition will ordinarily take the form of an aqueous composition containing the formula I compound in a concentration sufficient to impart the desired color to the metal ion treated hair.
  • it will be present in said hair dye composition at a concentration in the range of from about 0.1% to about 5% by weight based on the total weight of said composition with the preferred range being from about 1% to about 2% on the same weight basis.
  • the formula I compound may be applied to hair over a wide range of pH, e.g. from about 4 to 10. However, exceptionally good results are obtained with a pH range of about 5 to about 9, with the preferred range being from about 5 to about 7.
  • an oxidant composition is prepared which will be mixed with the hair dye composition containing the aminoalkyl- or aminohydroxyalkyl-catechols just before use to form a hair dye composition now containing the oxidant as well as the catecholamine.
  • Any of a variety of oxidants may be employed for the purposes of the present invention. By way of example, mention may be made of the following: hydrogen peroxide, persulfate (Na or K salt), percarbonates (Ba, Na, or K salts), periodate (Na or K salts), etc.
  • the oxidant is selected from the group consisting of a peroxide (e.g. H 2 O 2 , benzoyl peroxide, or urea peroxide), an iodate (i.e. IO 3 ), a persulfate, a periodate or combinations thereof.
  • a peroxide e.g. H 2 O 2 , benzoyl peroxide, or urea peroxide
  • an iodate i.e. IO 3
  • a persulfate e.g. Na, K, Li
  • alkaline earth metal e.g. Ca, Ba, Ti
  • the oxidant serves to accelerate even further the rate of the color formation beyond the rapid increase already caused by treating the hair with a metal-ion.
  • the concentration of the oxidant contained in the hair dye composition may vary somewhat. Generally the oxidant will be present in said composition at a concentration in the range of from about 0.05% to about 3% by weight based in the total weight of of the hair dye composition with the preferred range being from about 1% to about 2% on the same weight basis.
  • the hair dye composition used in the practice of this invention may also contain a variety of adjuvants commonly used in the hair dye art to facilitate the dyeing of the hair or that will improve the organoleptic qualities of the composition.
  • adjuvants commonly used in the hair dye art to facilitate the dyeing of the hair or that will improve the organoleptic qualities of the composition.
  • dye penetration enhancers such as phenoxyethanol, benzyl alcohol, isopropanol and others, can be successfully employed.
  • the term "hair dye composition” refers both to the simple formula I compound compositions and to the simple formula I compound compositions to which have been added the oxidant compositions. Accordingly, the final composition employed in practicing the process of this invention may also contain the adjuvants present in the simple aminoalkyl- or aminohydroxyalkyl-catechol composition or the adjuvants contained in both the simple aminoalkyl- or aminohydroxyalkyl-catechol composition and in the oxidant system.
  • the term "functioning metal ions” means any metal ion which accelerates the formation of melanin-like materials from the aminoalkyl- or aminohydroxyalkyl catechols. Salts of any of a variety of metals, which are preferably water soluble, may be employed for this purpose.
  • the metallic moieties of the salts that may be used in accordance with the present process the following may be mentioned: copper (e.g. Cu +2 ), titanium (e.g.
  • anionic moieties of these salts may be exemplified by such anions as sulfate, lactate, tartrate, acetate, citrate, nitrate and chloride. Again, this listing is not exhaustive of those anions of the metal salts employable in this invention.
  • salts which may be used in the pre-treatment of hair according to the present invention the following salts may be mentioned CuSO 4 , Ti(lactate) 2 , Fe(NO 2 ) 3 , FeSO 4 , K 3 Fe(CN) 6 , Pb(acetate) 2 , Cu(II) (Citrate), ZnSO 4 , NiSO 4 , Co(acetate) 2 , Ag(Nitrate), Mn(nitrate) 2 , Mn(Cl) 2 , etc.
  • the salts used in accordance with the present invention will ordinarily be applied to the hair from a composition containing the same which will usually be an aqueous composition.
  • concentration of the metal salt contained in this composition will vary somewhat, but generally will fall into the range of from about 0.001% to about 2% by weight based on the total weight of the metal salt composition, with the preferred range being from about 0.01% to about 1% on the same weight basis.
  • a convenient way of applying the metal salt is from a shampoo composition.
  • the metal salt composition in addition to detergents will also contain the adjuvants found in shampoo compositions. These include such items as amides, fatty acids, cocamidopropyl betaine, fragrance, preservatives, etc.
  • the hair on the human head is contacted with a metal salt containing composition as described above.
  • the metal salt concentration will be in the range from about 0.001% to about 5%.
  • This composition is allowed to remain in contact with the hair for a period of from about 1 minute to about 45 minutes; preferably from about 5 minutes to about 15 minutes.
  • the hair can then be shampooed.
  • This process will ordinarily be carried out at room temperatures although elevated temperatures may be employed, such as those which can be achieved with commercial hair dryers.
  • the hair is contacted with a solution of the formula I compound (e.g. 0.05% to 2% solution).
  • the pH of this composition may vary but typically it will be in the range of from about 5 to about 7.
  • the length or duration of application may vary somewhat depending on the results desired. Usually, however, this will be in the range of from about 5 to about 15 to 30 minutes.
  • Dyeing may be accomplished at any of a variety of temperatures. Preferably temperatures will be close to room temperatures (e.g. from about 20° C. to 35° C.). However, under some circumstances it may be advantageous to carry out this procedure at an elevated temperature, for example that achieved with commercial hair dryers.
  • an Fe ++ salt may be mixed with epinephrine to form a solution having a pH from about 5 to 7.
  • This composition may be used to dye hair that has been previously treated with a Cu ++ or Fe +3 salt. Treatment of the latter kind for a period of 20 to 30 minutes gives a medium golden brown dyeout.
  • the significant advantage to this method is the lack of any added oxidant or potential oxidant such as IO 3 , persulfate, or the like.
  • oxidant or potential oxidant such as IO 3 , persulfate, or the like.
  • the formula I compound solution may be mixed, for example, with 0.1 to 3% of an oxidant such as peroxide (e.g. hydrogen peroxide, benzoyl peroxide, or urea peroxide), persulfate (as the sodium or potassium salt), or a perhalite (e.g. periodate, perchlorate, or perborate) immediately prior to application to hair previously treated with a metal salt.
  • an oxidant such as peroxide (e.g. hydrogen peroxide, benzoyl peroxide, or urea peroxide), persulfate (as the sodium or potassium salt), or a perhalite (e.g. periodate, perchlorate, or perborate) immediately prior to application to hair previously treated with a metal salt.
  • peroxide e.g. hydrogen peroxide, benzoyl peroxide, or urea peroxide
  • persulfate as the sodium or potassium salt
  • a perhalite e.g. periodate, per
  • the hair dye composition employed contains both anaminoalkyl- or aminohydroxyalkyl-catechol and an oxidant this will generally be prepared first prior to the application to the hair.
  • a dye concentrate containing an aminoalkyl- or aminohydroxyalkyl-catechol will be mixed with an oxidizing composition containing one or more oxidants to obtain the hair colorant formulation.
  • the dye concentrate employed will contain an aminoalkyl- or aminohydroxyalkyl-catechol in the concentration range of from about 0.1% to about 5% by weight based on the total weight of the dye concentrate with the preferred concentration following in the range of from about 1% to about 2% on the same bases.
  • the oxidizing composition will contain the oxidant component or components in a concentration in the range of from about 1% to about 6% by weight based on the total weight. In this case the preferred concentration range is from about 1% to about 2% by weight based on the total weight of the oxidizing composition.
  • To prepare the hair colorant formulation i.e., the composition containing both an aminoalkyl- or aminohydroxyalkyl catechol and one or more oxidants, from about 0.5 to about 2 parts by weight of the oxidizing composition per part of dye concentrate will be mixed with each other just prior to use.
  • the colors obtained on hair from the exposure of metal salt pre-treated hair to an aminoalkyl- or aminohydroxyalkyl-catechol composition with or without an oxidant range from light to brown to black. It is sometimes advantageous to lighten the dark dyeouts to a golden brown or a dark brown.
  • an oxidizing agent such as an aqueous H 2 O 2 solution in which the concentration of the H 2 O 2 in said solution is in the range of about 0.1% to about 6% by weight based on the total weight of the aqueous composition and having an alkaline pH (e.g., pH 9 has been found to be quite suitable).
  • the hair is quickly lightened by saturating said aminoalkyl- or aminohydroxyalkyl-catechols dyed metal salt treated hair with this oxidizing solution for about 5 minutes to about 10 minutes and then rinsing the hair.
  • Solution A is made up by dissolving 2% dopamine (wt/wt) (i.e. 3,4-dihydroxyphenyethylamine) at pH 7 in buffered water containing 1% (wt/wt) of iodate (IO 3 , either the sodium or potassium salt).
  • a metal-salt solution is made by dissolving 0.04M copper sulfate in a solution of 1% monoethanolamine (vol/vol) in water and then treating blended grey hair in this solution for 5 minutes. The hair is then rinsed with water and patted dry. Next the hair swatch is treated for 15 minute in solution A for 15 minutes to give a of dark brown dyeout with yellow hues.
  • the prior art which does not use a metal ion requires 45 to 90 minutes to obtain dark grey to black dyeouts.
  • compositions are set out in Table I. These compositions were used in procedures which were substantially similar to that described above, except that the reagents and other parameters used were those listed in the table.
  • Table II sets forth another set of reagents.
  • the metal-salt solutions were applied for about five minutes.
  • the catecholamines were applied for about 10 minutes.
  • the resultant colors are given in the tables.

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US07/193,694 1988-05-12 1988-05-12 Coloring hair with aminoalkyl-or aminohydroxyalkyl-catechols Expired - Lifetime US4904274A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US07/193,694 US4904274A (en) 1988-05-12 1988-05-12 Coloring hair with aminoalkyl-or aminohydroxyalkyl-catechols
CA000573005A CA1325772C (fr) 1988-05-12 1988-07-26 Procede pour la coloration des cheveux a l'aide de compositions aminoalkyl- ou aminohydroxyalkylcatechol
MYPI89000211A MY104950A (en) 1988-05-12 1989-02-21 Process for coloring hair with aminoalkyl or aminohydroxyalkyl catechol compositions.
AT89301919T ATE107500T1 (de) 1988-05-12 1989-02-27 Verfahren zum haarfärben mit aminoalkyl- oder aminohydroxyalkylcatecholzusammensetzungen.
EP89301919A EP0341808B2 (fr) 1988-05-12 1989-02-27 Procédé de coloration des cheveux par des compositions contenant un aminoalkyle ou un aminohydroxyalkyle catéchol
ES89301919T ES2056202T3 (es) 1988-05-12 1989-02-27 Procedimiento para colorear el cabello con composiciones aminoalquil o aminohidroxialquil catecol.
DE68916319T DE68916319T3 (de) 1988-05-12 1989-02-27 Verfahren zum Haarfärben mit Aminoalkyl- oder Aminohydroxyalkylcatecholzusammensetzungen.
JP1052186A JPH01290618A (ja) 1988-05-12 1989-03-06 アミノアルキル又はアミノヒドロキシアルキルカテコール組成物による毛髪染色方法
KR1019890006359A KR950005117B1 (ko) 1988-05-12 1989-05-11 아미노알킬 또는 아미노히드록시알킬 카테콜로 조성물로써 두발 착색용 조성물

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US07/193,694 US4904274A (en) 1988-05-12 1988-05-12 Coloring hair with aminoalkyl-or aminohydroxyalkyl-catechols

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US (1) US4904274A (fr)
EP (1) EP0341808B2 (fr)
JP (1) JPH01290618A (fr)
KR (1) KR950005117B1 (fr)
AT (1) ATE107500T1 (fr)
CA (1) CA1325772C (fr)
DE (1) DE68916319T3 (fr)
ES (1) ES2056202T3 (fr)
MY (1) MY104950A (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4940318A (en) * 1988-11-03 1990-07-10 Itek Corporation Gradient membrane deformable mirror having replaceable actuators
US5042987A (en) * 1990-09-11 1991-08-27 Clairol, Inc. Method for reducing scalp staining in hair dyeing processes involving a metal ion pretreatment step
WO1993005759A1 (fr) * 1991-09-26 1993-04-01 Bristol-Myers Squibb Company Procede et kit servant a la teinture des cheveux
US5273550A (en) * 1991-09-26 1993-12-28 Clairol Incorporated Process and kit for dyeing hair
US5368610A (en) * 1993-04-20 1994-11-29 Clairol Incorporated Use of metal salts and chelates together with chlorites as oxidants in hair coloring
US5441542A (en) * 1991-09-26 1995-08-15 Clairol Incorporated Process and kit for post-oxidative treatment of permanently dyed hair
WO1996005799A1 (fr) * 1994-08-18 1996-02-29 Henkel Kommanditgesellschaft Auf Aktien Teinture pour cheveux
US5584889A (en) * 1993-12-27 1996-12-17 Clairol Incorporated Oxidative hair dyeing process with dihydroxybenzenes and aminoethanethiols
US5603734A (en) * 1993-12-27 1997-02-18 Clairol Incorporated Hair dyeing with persulfate oxidants and catechols
US5628799A (en) * 1991-09-26 1997-05-13 Clairol Incorporated Hair dying methods and kits which contain a dopa species, reactive direct dye, and a ferricyanide oxidant
US5792220A (en) * 1997-05-16 1998-08-11 Bristol-Myers Squibb Company Dyeing hair with melanin procursors in the presence of iodate and peroxide
US20090320215A1 (en) * 2006-08-10 2009-12-31 Jack Massoni Catalyzed air oxidation haircolor
US8366791B1 (en) * 2011-09-02 2013-02-05 Warner Babcock Institute Formulation and method for hair dyeing
US8828100B1 (en) * 2013-10-14 2014-09-09 John C. Warner Formulation and processes for hair coloring
US20160184197A1 (en) * 2013-10-14 2016-06-30 Warner Babcock Institute for Green Chemistry Formulation and processes for hair coloring
CN114099359A (zh) * 2021-12-02 2022-03-01 台州学院 一种多巴胺-Fe2+多彩染发剂及染发方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2049826A1 (fr) * 1990-09-11 1992-03-12 Keith C. Brown Methode de reduction des taches sur le cuir chevelu
GB0911493D0 (en) 2009-07-02 2009-08-12 Univ Leeds Catalysed dye systems
EP2873412A1 (fr) 2013-11-13 2015-05-20 Unilever PLC Composition de coloration des cheveux et procédé de coloration capillaire
CN109846742A (zh) * 2019-02-12 2019-06-07 西南医科大学 一种多色无毒染发剂及其制备方法和染发方法
WO2025006080A1 (fr) * 2023-06-27 2025-01-02 Edulis Labs Inc. Système et procédés de modification des propriétés de surface de surfaces contenant de la kératine

Citations (1)

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Publication number Priority date Publication date Assignee Title
JPH0372836A (ja) * 1989-08-12 1991-03-28 Izumi Giken Kk 製麺カッター

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DE2028818A1 (de) * 1969-06-11 1970-12-17 The Gillette Co,, Boston, Mass. (V.St.A,) Verfahren zum Färben von Menschenhaar
US4453941A (en) * 1980-12-29 1984-06-12 Board Of Overseers Of Goshen College Composition and process for producing pigmentation in hair or skin

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0372836A (ja) * 1989-08-12 1991-03-28 Izumi Giken Kk 製麺カッター

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4940318A (en) * 1988-11-03 1990-07-10 Itek Corporation Gradient membrane deformable mirror having replaceable actuators
US5042987A (en) * 1990-09-11 1991-08-27 Clairol, Inc. Method for reducing scalp staining in hair dyeing processes involving a metal ion pretreatment step
WO1993005759A1 (fr) * 1991-09-26 1993-04-01 Bristol-Myers Squibb Company Procede et kit servant a la teinture des cheveux
US5273550A (en) * 1991-09-26 1993-12-28 Clairol Incorporated Process and kit for dyeing hair
US5279617A (en) * 1991-09-26 1994-01-18 Clairol Incorporated Process and kit for dyeing hair
US5279618A (en) * 1991-09-26 1994-01-18 Clairol Incorporated Process and kit for dyeing hair
US5441542A (en) * 1991-09-26 1995-08-15 Clairol Incorporated Process and kit for post-oxidative treatment of permanently dyed hair
CN1050992C (zh) * 1991-09-26 2000-04-05 布里斯托尔-米尔斯·斯奎布公司 染发的方法和配套染发剂
US5628799A (en) * 1991-09-26 1997-05-13 Clairol Incorporated Hair dying methods and kits which contain a dopa species, reactive direct dye, and a ferricyanide oxidant
US5368610A (en) * 1993-04-20 1994-11-29 Clairol Incorporated Use of metal salts and chelates together with chlorites as oxidants in hair coloring
US5603734A (en) * 1993-12-27 1997-02-18 Clairol Incorporated Hair dyeing with persulfate oxidants and catechols
US5584889A (en) * 1993-12-27 1996-12-17 Clairol Incorporated Oxidative hair dyeing process with dihydroxybenzenes and aminoethanethiols
US5980586A (en) * 1993-12-27 1999-11-09 Bristol-Myers Squibb Company Oxidative hair dyeing process with dihydroxybenzenes and aminoethanethiols
WO1996005799A1 (fr) * 1994-08-18 1996-02-29 Henkel Kommanditgesellschaft Auf Aktien Teinture pour cheveux
US5792220A (en) * 1997-05-16 1998-08-11 Bristol-Myers Squibb Company Dyeing hair with melanin procursors in the presence of iodate and peroxide
US20090320215A1 (en) * 2006-08-10 2009-12-31 Jack Massoni Catalyzed air oxidation haircolor
US7758659B2 (en) 2006-08-10 2010-07-20 Combe Incorporated Catalyzed air oxidation haircolor
US8366791B1 (en) * 2011-09-02 2013-02-05 Warner Babcock Institute Formulation and method for hair dyeing
US8828100B1 (en) * 2013-10-14 2014-09-09 John C. Warner Formulation and processes for hair coloring
US20160184197A1 (en) * 2013-10-14 2016-06-30 Warner Babcock Institute for Green Chemistry Formulation and processes for hair coloring
US9522102B2 (en) * 2013-10-14 2016-12-20 Warner Babcock Institute For Green Chemistry, Llc Formulation and processes for hair coloring
CN114099359A (zh) * 2021-12-02 2022-03-01 台州学院 一种多巴胺-Fe2+多彩染发剂及染发方法

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DE68916319D1 (de) 1994-07-28
JPH01290618A (ja) 1989-11-22
EP0341808B2 (fr) 1996-12-18
KR890016960A (ko) 1989-12-14
CA1325772C (fr) 1994-01-04
EP0341808B1 (fr) 1994-06-22
DE68916319T3 (de) 1997-05-22
KR950005117B1 (ko) 1995-05-18
ATE107500T1 (de) 1994-07-15
EP0341808A1 (fr) 1989-11-15
ES2056202T3 (es) 1994-10-01
DE68916319T2 (de) 1995-01-05
MY104950A (en) 1994-07-30

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